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2-Arachidonoyl Glycerol

Catalog No.GC16403

2-Arachidonoyl Glycerol Chemical Structure

An endogenous agonist of the cannabinoid (CB) receptors CB1 and CB2

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1mg
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5mg
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10mg
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25mg
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Sample solution is provided at 25 µL, 10mM.

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Background

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the cannabinoid (CB) receptors CB1 and CB2 (Kis = 25.3-472 and 145-1,400 nM, respectively).[1],[2],[3] Unlike arachidonoyl ethanolamide, 2-AG is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol (MAG) found in rat brain.[1],[4] Formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol (DAG) lipase.1 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism.2 2-AG is metabolized in vitro by MAG lipase and fatty acid amide hydrolase (FAAH), with MAG lipase likely being the principle metabolizing enzyme in vivo.[5]

Reference:
[1]. Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388(6644), 773-778 (1997).
[2]. Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J. Biol. Chem. 274(5), 2794-2801 (1999).
[3]. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 6(8), 635-664 (1999).
[4]. Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Letters 429(2), 152-156 (1998).
[5]. Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proceedings of the National Academy of Sciences of the United States of America 99(16), 10819-10824 (2002).

Chemical Properties

Cas No. 53847-30-6 SDF
Synonyms 2-AG
Chemical Name (5Z,8Z,11Z,14Z)-1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate
Canonical SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(OC(CO)CO)=O
Formula C23H38O4 M.Wt 378.55
Solubility 10mg/mL in DMSO, miscible in ethanol Storage Store at -80°C;protect from light
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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